Hydrochloric Acid → 2-Hydroxy-6-methyl-3-(trifluoromethyl)benzoic acid

HRID 2076634Notes

Reaction equation

HRID 2076634 reaction equation
Cl([O-])=O.[Na+].O.P([O-])(O)(O)=O.[Na+].[OH:12][C:13]1[C:20]([C:21]([F:24])([F:23])[F:22])=[CH:19][CH:18]=[C:17]([CH3:25])[C:14]=1[CH:15]=[O:16].CC(=CC)C.S([O-])([O-])(=[O:33])=S.[Na+].[Na+].Cl>C(O)(C)(C)C.O1CCOCC1>[OH:12][C:13]1[C:20]([C:21]([F:22])([F:23])[F:24])=[CH:19][CH:18]=[C:17]([CH3:25])[C:14]=1[C:15]([OH:33])=[O:16]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 105532-Methyl-2-buteneHCID 24477Sodium ThiosulfateHCID 516949Sodium Phosphate, Monobasic, MonohydrateHCID 23668197Sodium ChloriteHCID 860881252-Hydroxy-6-methyl-3-(trifluoromethyl)benzaldehyde

Product 1

HCID 671190402-Hydroxy-6-methyl-3-(trifluoromethyl)benzoic acid

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolventHCID 312751,4-DioxaneSolvent

Procedure

After an aqueous solution (40 ml) of sodium chlorite (6.0 g, 66.3 mmol) and sodium dihydrogenphosphate monohydrate (6.0 g, 43.5 mmol) was added dropwise to a solution of 2-hydroxy-6-methyl-3-(trifluoromethyl)benzaldehyde (4.65 g, 22.8 mmol) obtained in Example (28-2) in a mixture of tert-butyl alcohol (90 ml), 1,4-dioxane (30 ml) and 2-methyl-2-butene (30 ml), the mixture was stirred at room temperature for 1 hour. After the reaction mixture was cooled with ice and a 5% aqueous sodium thiosulfate solution was added thereto, the mixture was poured into 0.5N hydrochloric acid and extracted with ethyl acetate (twice). The organic layer was successively washed with water and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The residue obtained by removing the solvent under reduced pressure was crystallized using ethyl acetate and n-hexane to give 2-hydroxy-6-methyl-3-(trifluoromethyl)benzoic acid as a colorless compound (4.21 g, yield: 84%).

Workup

  1. temperatureAfter the reaction mixture was cooled with ice
  2. extractionextracted with ethyl acetate (twice)
  3. washThe organic layer was successively washed with water
  4. dry with materiala saturated aqueous NaCl solution and dried with anhydrous sodium sulfate
  5. customThe residue obtained
  6. customby removing the solvent under reduced pressure
  7. customwas crystallized

Sources & evidence

ORD record
ord-9bdff891cf724446853cd98af5286e4a
Source dataset
uspto-grants-2011_04
Patent number
US07923573B2

Reaction notes

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